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Background: Salvinorin B ethoxymethyl ether (Symmetry) is a novel and unusually potent salvinorin that has not previously been tested in humans. Methods: Symmetry was synthesized and given in doses of 10 &micro>g to 400 &micro>g to four test subjects. Effects were measured through semi-structured interview and administration of the Peak Experience Profile. Results: Symmetry was extraordinarily potent, psychoactive at the minimum doses taken. It produced geometric visions and ego loss at higher doses, and also induced a feeling of foreboding. Conclusions: Symmetry is a salvinorin derivative of unusual potency that is worthy of further investigation but nevertheless is unlikely to become popular.

FIGURE 1

INTRODUCTION

Many readers of The Entheogen Review will be familiar with the largely legal psychedelic Salvia divinorum, an entheomedicinal sage originally used by the Mazatec Indians of Oaxaca, Mexico. This plant's active compound, salvinorin A (Ortega et al. 1982), is the most potent naturally occurring psychedelic known, producing clear effects at doses of one milligram or less when vaporized (Siebert 1994). Salvinorin A acts at the kappa opioid receptor (Roth et al. 2002), and since most previously known potent opioids have been alkaloids, not diterpenoids, this discovery has excited scientists considerably. In recent years, over a hundred derivatives of salvinorin A have been synthesized in hopes of producing new medicines (Prisinzano & Rothman 2008). A few of these derivatives have had interesting properties, but most are simply disappointing, less-potent imitations of salvinorin A itself. Other salvinorins and related compounds have also been extracted from the plant (Shirota et al. 2006), but again, these compounds are less potent at opioid receptors than salvinorin A.

Our attention was therefore caught by a report of a derivative that was actually more potent: salvinorin B methoxymethyl ether (Lee et al. 2005). This in vitro result was later confirmed in mice studies, which also showed that the drug appeared to last longer than salvinorin A (Wang et al. 2008). Then came another report that a slight modification to this compound made an even stronger drug, salvinorin B ethoxymethyl ether (Munro et al. 2008), which appeared to be about ten times as potent as salvinorin A in vitro (Figure 1). If this turned out to be true in humans as well, it would make salvinorin B ethoxymethyl ether (henceforth referred to as "Symmetry") one of the most potent known psychedelics, comparable to the legendary LSD. Now thoroughly intrigued, we decided to find out for ourselves.

METHODS

Four subjects (Alpha through Delta) were recruited to participate in the bioassay. All were free of comorbid medical and psychiatric conditions, had extensive prior experience with psychedelic drugs, and were not allergic to salvinorin A.

Set:

As with other visionary plants and drugs, users of Salvia divinorum and salvinorin A sometimes report contacting "plant spirits," "teachers," or "entities" when under the influence (see, for example, Kathleen Harrison's encounter with the spirit of La Pastora; Harrison 2000). One of our subjects felt strongly that the Symmetry needed to be "honored" before she took it, so we went along with this approach because there seemed no harm in it, and we were also curious if such psychological suggestion might increase the chance of some sort of entity encounter. Participants were instructed that they would be taking a new derivative of the "plant teacher" salvinorin A, with which everyone was familiar. In order to prepare, each participant was instructed to: 1) Rent two nature documentaries and watch them over the two days prior to the experiment, in order to increase awareness of and appreciation for the natural world; 2) View old photo albums, paying particular attention to pictures of family; 3) Write an autobiography (not for sharing) of no more than two pages, in order to promote introspection; 4) Read two FAQs from Erowid (Gnosis et al. 1996; Salvia Authors 2006); and 5) Think of two questions for any potential Symmetry "entity" to answer.

Setting:

A living room with windows, a carpet, sofa, chairs, and many plants. Candles were lit, in addition to diffuse incandescent lighting, and soft ambient music was played. Participants had been asked to bring toys to share and drums to play, although none were subsequently used. Standard rules applied: respect absolute confidentiality, ask before changing any aspect of the environment, respect each participant's veto power over activities, and no hitting, sex, or co-ingestion of other inebriants.

Drug:

Salvinorin B ethoxymethyl ether (Symmetry) was synthesized from salvinorin B by the published procedure (Munro et al., 2008; see reference for URL). This should only be attempted by trained chemists in well-equipped labs. The reagent used, chloro-methyl ethyl ether, can give you cancer not only if it touches your skin, but also if you breathe the fumes. For dosing, a [10 mg/ml] solution of the compound in acetone was prepared. The desired doses were added to small pieces of cigarette paper by microsyringe and allowed to dry in a warm airflow.

Measures:

Subjects were interviewed the next day via an open-ended format that elicited details of their experience in a nondirective manner. The interview also included questions about the nature of their visionary experiences, what the positives and negatives were, whether contact with any "entities" had occurred, and what they would change about the experimental design in order to improve the experience. A one-month follow-up was conducted that consisted of two questions: 1) "Are you glad you had the experience?" and 2) "Would you do it again?"

The Peak Experience Profile (PEP) is a 180-item self-administered questionnaire originally developed by Walter Pahnke in 1962 for his "Good Friday" experiment and revised over the years by Pahnke, Franco Di Leo, Stanislav Grof, A.A. Kurland, J.C. Rhead, William Richards, and Richard Yensen (Richards et al. 1977; Doblin 1991). It has been used in many psychedelic drug studies to assess the degree and quality of visionary experiences. Each subject completed the PEP within a week of the experience.

Bioassay:

After a light meal, at a predetermined time, the room was "smudged," and subjects participated in a modified version of the "Four Winds Ceremony," each subject taking one of the four compass points, honoring the drug and the experience they were about to have. The cigarette paper containing the Symmetry was then smoked using the flame from a butane lighter. Bioassay structure was based largely on the protocol popularized by Alexander Shulgin (Shulgin et al. 1986; Shulgin & Shulgin 1991), but for logistical reasons, a day was not left between successive doses.

FIGURE 2: PEP subscales by dose. Reactivity was fairly constant between subjects, except at the lowest dose; this measures a subject's tendency to exaggerate responses in a nonspecific manner. Negative, or "nadir" experiences consistently exceeded positive mood changes. [Note: The apparent "heart" symbol on #10 line is merely a super-imposition of a square and "x" symbol.]

RESULTS

Despite instructions to the contrary, none of the participants had watched nature videos or written his or her autobiography, although all brought questions to ask any potential entity that they might encounter. The drug was quite potent, with one subject "alerting" at 10 &micro>g, another at 50 &micro>g, and the other two experiencing undeniable psychoactive effects at 50 &micro>g. Psychedelic effects increased rapidly and linearly by dose (Figure 2), with the exception of one subject who appeared unusually tolerant to its effects. The unpleasantness of the experience appeared unrelated to dose, and consistently exceeded positive effects at all doses. There appeared to be little experience of personal insight despite otherwise dramatic effects (Table 1). Subjective results of bioassays were as follows:

ALPHA

Written down the next day based on notes.

(T:0:00 min) 10 &micro>g
As this is the first time this drug has been tried, and we suspect based on mouse studies that it may be even more potent than the already potent salvinorin A, I opt to start with a low dose. Within seconds of smoking, an undeniable shift in my consciousness occurs, a slight "trippy" feeling, but without any noticeable alteration in perception, thought content, or process.

(T:0:15 min) 50 &micro>g (100 &micro>g total)
I am sweating profusely--when I run my fingers through my hair, they come away wet. There is a mild sensation of--not heaviness--but being "pulled down" into my chair. I feel a slight mental fog, as can occur with alcohol, but no temporal lapses or difficulties communicating. There are no noticeable effects on music perception or tactile sensation, but closed-eye visuals are now undeniable, albeit frustratingly indistinct--fragmented, colored spoke-like patterns.

(T:0:20 min) 100 &micro>g (200 &micro>g total)
Again, a deepening and intensification of all previous phenomena, but no qualitative shift. Open-eye visuals are now apparent: sharp colored borders to objects with a suggestion of palinopsia (visual echoes). I am starting to wonder if I am somehow inhaling wrong and not getting the full effects of the drug, or else leaving too much time between successive doses, as the effects appear to peak within a minute then diminish rapidly.

(T:0:25 min) 200 &micro>g (400 &micro>g total)
According to observers, I commented on the intensity of the trip, laughed uproariously, and conversed--coherently at first, but rapidly incorporating nonsense words and syllables. Then I paused, leaned forward and asked, apropos of nothing, "Did you say something... symmetry?" It seemed as if I had meant it in the sense of "symmetrical." (It was decided on the basis of this first communication from the beyond to name the drug "Symmetry.") Later sentences rapidly degraded into complete babble. My head was observed to retract, and my face froze into a frighteningly blank expression as if I were having a stroke. My hand adopted a strange pose and waved around very slowly, alternately creepily awkward and graceful. I remembered none of this.

BLAM! I am trapped like a fly in amber, in a geometric space that is so different from ordinary reality as to be indescribable. The overall feeling is one of "stuckness," together with slow and inexorable grinding. As I come to, I realize that my perspective is arbitrary and that I can shift it at will to different points in the cavitating matrices in which I am embedded. With that comes the realization that the presence of a perspective implies an "I" to have that perspective. This is a new change; in fact, I have just emerged from an indeterminable period of total ego loss. The experience was ineffable, but I will attempt to describe it using crude analogies in the blunt tool that we call language.

Imagine a sheet of sand going over a cliff, or rather a rapidly receding ledge under sand such that the sand drops in a sheet as the ground vanishes under it. It is impossible to determine whether the sand is moving forward over the edge, or if the edge is moving backward under the sand, but either way the edge itself is a one-dimensional line defined by a two-dimensional surface moving over the contour of an unseen three-dimensional object. That line can wiggle or ululate or assume configurations other than a knife-edge, so technically it is not one-dimensional, but the line doesn't know that. Now add two to every dimension--I was perceiving all three-dimensional objects in my world as four-dimensional surfaces contouring a five-dimensional object (or objects) that I could not directly perceive.

Except that I wasn't actually perceiving any objects in my environment, it was my mind that I was perceiving, as a manifestation of the movement of a five-dimensional object through a four-dimensional membrane. Except, there was no "movement"; that's the term for the intersection of three-space with four-space, not four-space through five-space. It was completely atemporal. Hopes, dreams, fears, memories, habits, all the things that define us are creations of time; remove time and you remove everything that comprises the "me" of each of us--the ego is obliterated.

If that analogy makes no sense--and it cannot--then alternately, imagine two viscous and immiscible liquids in a clear cylindrical container, one denser than the other so that a distinct interface is visible between them. Trapped at that interface is a blob of food coloring. Now, spin the top layer of fluid. The blob elongates, grows thinner and thinner, less and less visible; eventually it is a layer only a molecule thick and cannot even be seen by the naked eye. Now stop the top layer, and spin it the other way. The blob re-coalesces--first visible as a long colored line that slowly grows thicker then abruptly retracts from both directions until the original blob is visible as a unitary sphere for a split second; then, as the liquid layer continues to spin, it elongates, thins, and disappears in the other direction (which, although opposite, looks exactly as it did when elongating in the first direction).

Now, imagine that this cylinder contains an infinite number of layers of immiscible liquids, all spinning, each layer containing one or more blobs in various stages of coalescence. By arranging the blobs correctly, and timing the spinning of the layers, one could make it seem as if one blob was moving up and down and right and left through the layers, in an arbitrarily complicated path, rather than many different blobs coalescing and de-coalescing in pattern. These blobs are everything we see in the three-dimensional world, and in our consciousness as well. Again, the analogy is inadequate, because the geometry is no longer there, and spinning implies movement, which assumes time, which didn't exist, but I am at a loss to find words to express such atemporality since time is so embedded in our thoughts and language.

The eternal moment in which I was trapped seemed to be passing. As a sphere passing through a plane appears from a two-dimensional perspective to be a point that rapidly expands into a circle, slows, reverses course, shrinks rapidly to a point, and disappears forever, so it seemed that the moment I was in was rapidly constricting as it moved out of the four-dimensional plane I was in. Fleetingly, it occurred to me that I might be left in a grey, timeless limbo. But to my surprise another moment followed, rapidly expanding, somewhat overlapping the first one; more moments followed in steadily quicker succession (again the "time" implied here is a metaphor, as they weren't really "quicker") and I rejoined the stream of time. It was now hard for me to remember what had happened to me during the period of ego loss, but I did remember the thoughts I'd had about it in the atemporal period I had just left. The room reformed around me, three expectant faces looking at me.

The initial comedown was rapid--like a sphere passing though a plane--followed by a slow decline. I ate half a bunch of juicy green grapes and enjoyed them. Slight confusion remained; I was unable to keep track of dose and timing for the other participants with nearly the precision that I had planned. I was still experiencing mild visuals until two hours later. I had no difficulty sleeping, woke up feeling normal the next morning, and did not remember my dreams.

I was shaken by the experience and had no desire to re-dose. There had been no sense of a "presence" or guiding spirit; there were no answers to the questions that I had formulated--in fact, they seemed completely irrelevant given the experience that I had just been through.

(T:0:06 min) 200 &micro>g (350 &micro>g total)
Objects replicate over surrounding surfaces. All visible surfaces, including other people, seem to be connected parts of the same object, like a textured blanket thrown over reality.

Replication continues until my entire visual field is filled with repetitive motifs, resembling vast bookshelves of books bound in fresh skin. The geometry of the room has changed and contracted. My awareness of my body as a separate entity is gone, but I feel a strong physical rush, accompanied by growing paranoia. Someone is monitoring me, and I must act sober. But this is clearly impossible--the real world is now invisible; I have no idea where I'm looking, what posture I'm in, what I'm saying. This intensifies the paranoia. I attempt to sit still and remain silent, but don't know if I'm succeeding.

The geometry of the room slowly expands to normal. I hear voices; distinct objects appear. Normality returns, but I am definitely confused and physically clumsy.

(T:0:30 min)
Slight hallucinations are still apparent.

(T:2:00 hours)
Sober but shaken. One wonders who would see anything in this experience.

GAMMA

Recorded the day after the trip, then transcribed.

This protocol was similar to the preceding one--starting with 50 &micro>g, then at two-minute intervals, 100 &micro>g, 200 &micro>g, 400 &micro>g, then between two and four more doses of 200 &micro>g, the precise number of which eluded the recollection of all of us later, for a total dose of 1150-1550 &micro>g.

In the beginning, the first thing I noticed with eyes closed were these whirling, snowflake-like things; they were very cool--they were in the pattern of the "Tree of Life," the flower pattern--they were laughing. I know this makes no sense, but I started laughing because they were laughing because I knew what they were: an underlying structural pattern.

Then I noticed feeling as if I was disoriented as to which direction was up, and that's when I knew that it was going to be very interesting if I took more. It felt as if I was holding on to a monkey bar, but I couldn't tell if I was upside-down or... I don't know, it was as if there was a space in front of me. Then there was a space that I don't remember very well, in which I felt confused but knew that I wanted to smoke more. I was given more to smoke, but I can't remember too much about it.

Then the patterns became more colorful, but not like... they were geometric. Well, they weren't really geometric, they were somewhat irregular, but they were patterning. There seems to be some break in time during which I can't remember what happened. But something that I heard in the music gave me a clue as to... I don't know... it's kind of personal--it's more like certain experiences I'm trying to create more of in my life, and how to do that.

I definitely remember feeling confused on the way up, incapable of communicating with any of you. I remember I was laughing because that kid in the video, Alex [the star of some witless YouTube Salvia self-administration videos that we had watched earlier] said that the more you smoke Salvia, the easier it is to hold it in your lungs--and I completely got what he was saying. The more high I was, the easier it was to smoke more, which was useful because I'm not very good at smoking anything! Did I have a four-hundred mic dose? No! That was in that incomprehensible period... as soon as you told me something, it immediately left my brain. If I said "yes" right away then that was fine, but if I didn't say "yes" right away then I probably forgot what you asked. Did you have to repeat questions to me?

Then it segued into this weird snail-shell of a space--that's what I was talking about. It was like being in an Escher-like space, with arches that vaulted up overhead and could connect different points in time across my life. That's what I saw. It wasn't as if I was watching a movie seeing things; I was re-experiencing them. But mostly experiences like walking along the street I lived on as a child, looking up at the sky and the trees overhead that I could see. I never think about this now, but I could actually see what it looked like at that age, like it was a memory I never think to recall, because it seems trivial. I felt that there was a presence of my brother's best friend's father! It's somehow related to [Alpha] too (laughs)--I felt that over where you were located was somehow related to where he was located in the space. I remember thinking about you at that moment, thinking that your description of this experience was pretty... er... even though I was not experiencing it quite the same way you were, it made a lot of sense, what you were saying, how you were describing it. There's a lot more, but it's all details.

FIGURE 3: Visual depiction of Symmetry experience.

Like what? Well, when I was laughing at the snowflakes, it wasn't my complete visual field; there was a jagged edge running though the vision and everything to the right side of the jagged edge was black space [see Figure 3]. And I had the sensation that everything on that side of my body was... there was nothing going on over there. But everything to the left side was very patterned and interesting. Was it a line? No, it was off to the right; it was completely irregular; it wasn't geometric at all; it didn't have a pattern; it was kind of uncomfortable. I remember thinking, "Why is there this line? Why is this vision incomplete?" It seemed very odd.

And then there were a lot of strange body sensations; a feeling like I was just an outline of myself. The cat touched me at one point; it felt really weird! I knew it was the cat, but it didn't feel very cat-like! The texture was like touching silk but getting cotton. It felt a little more coarse. At any point on my body that was touching something else in the room, like the couch or the floor or itself, there was an uncomfortable amount of pressure, which is why I think that the next time I do it I'll try to change how I'm sitting. I think I may have said this when I came out of it, but it would be ideal to be floating. That would be amazing. A sensory deprivation tank? That would be great! That would be fascinating. Wow, I'd love to check that out.

I had questions but I forgot about them until afterwards. No answers came. I had a question about what form the [deleted] should take, and although I didn't get an answer, afterwards when I was thinking about it--still "salvia'd up" but not tripping hard--I thought about some of the concepts, and that the idea of toruses might be something worth pursuing. It was my own mind thinking about it, but it was inspired by the form of the wrap-around space. I didn't get the sense of an entity outside. I got the sense of curtains parting, delivery into an idea. I don't know where ideas come from, they just seem to arrive. But there wasn't a sense of, "Okay, impart to meee..." They just sort of appeared.

I've had a lot of experiences with Salvia, and many of them have been good, but some of them have not been very good. In those experiences I've had the experience of an entity, something pointing out to me what's going on. I feel a discomfort in my body unless I sit exactly right, and these "corrections" are very precise--make a tiny little adjustment here, and so on, until everything is right. There definitely feels like there is an outside entity that needs to be appeased with Salvia.

There was a lot more closed-eye stuff with Symmetry. Would I be able to tell which is which? I suspect yes, because this "posture correction" is so reproducible with Salvia. That's why I sat down on the floor, because I knew that if I wanted to sit up straight then I wasn't going to be able to do it on the couch. I expected that this was going to happen, and that I would have to sit up straighter, but that feeling was completely not there at all. I told you that I still wanted to change my position, that I wasn't perfectly happy with how I was oriented; I could feel my hands on my knees, and it didn't feel quite right, but I knew that if I put them on the floor then it wasn't really going to help. There was no way to get right! I'd like there to be a way to feel right.

What would I change going into it? I would probably take something to make my body intensely comfortable no matter what happened.

DELTA

Recorded the day after the trip, then transcribed.

(T:0:02 min) 50 &micro>g
The first thing I noticed was a bit of general light-headedness, a little tingling everywhere; I couldn't differentiate it from being mildly stoned--something like that. I couldn't tell if it was placebo. "Am I feeling something, or am I not?"

(T:0:04 min) 50 &micro>g (100 &micro>g total)
Then it was more--I definitely got some effects; the shadows were very strong and the walls... the spaces between the shadows were more orange--very orange, much more so than they normally were. Now that I can see this picture that's difficult to describe on the wall, the "Hope and Fear" picture (see Figure 4); the blue stuff looked more like a hologram, the blue bits look more silver and had a degree of depth, like a hologram jutting. And it was by far the most interesting thing on the wall! The rest just looked like shadows. And the tea mugs looked more orange. The glow seemed to have spread further.

(T:0:06 min) 50 &micro>g (150 &micro>g total)
It was a feeling of... it was not unpleasant, but I guess "foreboding" was the word you used. It was a sense that I didn't necessarily want it to be more. But because the effects were so relatively mild, I felt that even if the next one was worse, it probably wouldn't be worse to the point that I'd, I don't know, "freak out."

And then it really was just a linear increase on everything I had before. The shadows became more exaggerated; the hologram thing looked more like that. Then I remember looking around and realizing that everyone was here, and that I had entirely forgotten what was actually happening, and it was kind of amusing to realize that I'd been entertainment for other people. Very hallucinogenic because I'd completely forgotten that anyone was present! But I had the experience that I've had a couple of times on mushrooms--especially inside a room--that it was quite hard for me to imagine the room connected to an external space. Out through the windows looked very surreal, as if that was just a painting, and that there wasn't really anything outside that room. I didn't have any strong feelings of time distortion, but had you asked me to make any kind of judgment about future or past, I would have struggled. The room was spatially and temporally separated from anything else--forward or back, inside or outside--but not in an intense way.

When I closed my eyes I saw some small patterns--actually even when I went to sleep about an hour later, I had some small patterns, but only very minor, nothing with any shape. You then asked if I wanted more, and I really didn't (laughs). At the same time, I wasn't having a bad experience, but there was a sense of caution, like, "I really don't want more." It's hard to know whether that was the drug or whether that was something that I brought with it, because what you guys were reporting didn't sound very good. So in my mind I was thinking that if I took more and got into this next state, then that would be a disaster. "I want to try to avoid that so let's just stay here." Things weren't really jumping out at me crazy; I wasn't getting any massively vivid effects, just these discontinuities: "What was I doing again? Where's outside?" I felt like I was holding it together pretty well, but I was disoriented. And with the visuals and all the effects, I felt like a little bit more might be enough to lose my "grip," and the thought of that didn't appeal at all.

I didn't have any questions, but I didn't get a sense that if I'd had any questions... If anything there was less information rather than more information in the experience--a dulling and disconnect. So I feel like if I'd asked a question, the answer would either have made no sense or seemed even further disconnected.

How would I prepare differently? I don't know. I had some... not really bad paranoia experiences, but definitely in that dimension, when I was coming down. I remember looking at you all and thinking that you must think I'm crazy, that everyone was looking at me weird, and that I must look really weird. So I was somewhat hyper-self-aware. Had it been a higher dose, it would have been very unpleasant. But I knew to think, "Well, this is a drug state. Maybe it's true, but if so, I'll worry about it in five minutes' time." So it was okay. There weren't any positive vibes coming from the experience. The general emotional experience wasn't positive. Slightly unpleasant. So I don't know. This was a comfortable environment. I certainly wouldn't ever take Symmetry in an uncomfortable environment. Anything you could do to make yourself physically comfortable. Perhaps a more closed space--okay, this is a closed space. Something more safe then. More soft things. It's hard to say, but I wouldn't want to do it in a sterile laboratory environment, that's for sure.

DISCUSSION

Symmetry is a salvinorin derivative of extraordinary potency--threshold dose when smoked between 10 &micro>g and 50 &micro>g, with marked effects at 150 &micro>g to 300 &micro>g, potency rivaled only by a few synthetic compounds such as LSD and carfentanyl. By comparison, Jonathan Ott has noted threshold effects from vaporized salvinorin A to occur at 500 &micro>g, while Daniel Siebert reported a threshold of 200 &micro>g; in both reports, notable effects required more than one milligram (Ott 1995a; Siebert 1994). Effects from smoked Symmetry became noticeable within seconds, peaked in about a minute, and started to diminish rapidly after about five minutes, as with salvinorin A. However, unlike salvinorin A, a residual alteration in consciousness was still noticeable at 30 minutes; all subjects were back to baseline by two hours.

At low doses of 100 &micro>g to 200 &micro>g, spoked geometric closed- and open-eye visions, alterations in perspective, palinopsia, and foreboding predominated, and at higher doses, mental confusion, derealization, and more vivid geometric visions occurred. At 400 &micro>g, one participant had a full "plus-four" experience (Shulgin et al. 1986), although another took three times that amount without the same effect. The reason for this disparity is unclear, although interestingly, that subject considered salvinorin A to be her "drug of choice" and had much more experience with it than the rest of us put together. No subjects experienced any sort of "entity" contact or even sensed a presence of such entities, despite suggestions that they might, reporting instead a vague sense of foreboding, as if venturing beyond a door marked "Do Not Enter."

All participants at one-month follow-up reported "enjoying the experience" and being "willing to take it again." Symmetry may be of particular interest to mathematicians or theoretical physicists; nonetheless, if this first look is any guide, it is unlikely to gain enduring popularity as either a recreational drug or spiritual sacrament. •>